Dimethylformamide → 3-(5-Methoxymethoxy-4,6,7-trimethyl-1,3-benzoxathiole-2-yl)propanol

HRID 2308878Notes

Reaction equation

HRID 2308878 reaction equation
[H-].[Na+].CN(C)C=O.[OH:8][C:9]1[C:10]([CH3:24])=[C:11]([CH3:23])[C:12]2[O:16][CH:15]([CH2:17][CH2:18][CH2:19][OH:20])[S:14][C:13]=2[C:21]=1[CH3:22].[CH3:25][O:26][CH2:27]Cl>C1C=CC=CC=1.O>[CH3:25][O:26][CH2:27][O:8][C:9]1[C:10]([CH3:24])=[C:11]([CH3:23])[C:12]2[O:16][CH:15]([CH2:17][CH2:18][CH2:19][OH:20])[S:14][C:13]=2[C:21]=1[CH3:22]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 1275772-(3-Hydroxypropyl)-4,6,7-trimethyl-2H-1,3-benzoxathiol-5-ol

Product 1

HCID 148021913-(5-Methoxymethoxy-4,6,7-trimethyl-1,3-benzoxathiole-2-yl)propanol

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

340 mg of a 55% w/w oily suspension of sodium hydride was added to 20 ml of dimethylformamide, followed by 2.0 g of crystals of 3-(5-hydroxy-4,6,7-trimethyl-1,3-benzoxathiole-2-yl)propanol (prepared as described in Example 71), with ice cooling and under a stream of nitrogen. The reaction mixture was then cooled with ice for 30 minutes, after which it was allowed to react for 1 hour at room temperature; it then was again cooled with ice. A solution of 630 mg of chloromethyl methyl ether in 2 ml of benzene was then added dropwise, after which the temperature of the reaction mixture was gradually raised and the reaction mixture was allowed to react further for 20 hours at room temperature. The reaction mixture was then poured into water and extracted with benzene. The extract was washed with water and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was subjected to silica gel Lobar column chromatography. The title compound was obtained from the fraction eluted with a 9:1 by volume mixture of benzene and ethyl acetate.

Workup

  1. temperatureThe reaction mixture was then cooled with ice for 30 minutes
  2. customto react for 1 hour at room temperature
  3. temperatureit then was again cooled with ice
  4. temperatureafter which the temperature of the reaction mixture was gradually raised
  5. customto react further for 20 hours at room temperature
  6. extractionextracted with benzene
  7. washThe extract was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-865b03a475e84271a4e0ad98dfdb9056
Source dataset
uspto-grants-1987_09
Patent number
US04691027

Reaction notes

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